Oak Bluffs Vacation Rentals

Oak Bluffs is a beautiful peninsula on the north eastern coast of Martha’s Vineyard that is bordered by Nantucket Sound. Renting a vacation home in Oak Bluffs gives you so many options. Our list of vacations rentals include luxury waterfront properties with exceptional views of the sound and quaint Victorian homes that allow you to glimpse deeply into Martha’s Vineyard’s historic past. Vacationing in Oak Bluffs is like taking a trip back in time. Ocean air and private beaches make you feel as though you have Martha’s Vineyard all to yourself.

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Beautiful Oak Bluffs Home, Screened Porch & Open Porch, Association Tennis Courts, 4 bedrooms, 3.5 baths, Ideally Located just 2 miles to Town and Beach

Spacious contemporary home nestled in the lovely community of homes Meadow View Farms just on the outskirts of Oak Bluffs and 2 miles to town center and Oak Bluffs beaches....Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,820 - $11,750
June 2025
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 $11,750
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$9,750
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 $6,820
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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STEJE

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Property Details
Charming Oak Bluffs Home, Waterfront on the Lagoon, Patio & Deck Areas. Spectacular Views & Sunsets

Waterfront on the Lagoon! The highlight of this home is its breathtaking views across the lagoon and beautiful sunsets. Whether you're inside or outside on the deck or patio, you can...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$8,500 - $11,500
June 2025
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 $8,500
August 2025
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 $5,000
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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CURRM

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Property Details
Outstanding Designer Home, 15 Min Walk to Oak Bluffs Center, 4 Bedrooms each en suite with TV, Occupancy Limit 9

Stylish Dreamy Home on Dreamer's Way, less than a mile from the town center and beach area! The owners have left nothing out in the way of design and comfort in...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
4
Baths: 
4
Price Range:
$3,500 - $11,200
June 2025
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 $9,200
August 2025
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 $8,000
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Owner ACCEPTS 3 NIGHT MINIMUM STAYS, MEMORIAL DAY WEEKEND TO JUNE 16TH, AND SEPT 7TH TO THE END OF OCTOBER.

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MANUC

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Property Details
Hart Haven, Spacious Contemporary Colonial, Private Association Beach .8 mi from house, Private Association Tennis, 5 min walk from house

Located in the desirable enclave of homes known as Hart Haven just on the outskirts of Oak Bluffs Center, rental guests will surely enjoy this beautifully maintained home bordered by...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$10,000 - $11,000
June 2025
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 $10,000
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Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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GOLDF

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Property Details
Outstanding Oak Bluffs Summer Home with Heated Pool and Patio Surround, Screened Porch with Living and Dining Area, Association Tennis Courts.

MVVR Exclusive Listing:  Set in a quiet community of homes just on the outskirts of OB, this outstanding home provides a peaceful getaway yet is just a short drive to the...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
5
Baths: 
3
Price Range:
$5,500 - $10,500
June 2025
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Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Pool Heated to 80 July & August and the 1st week in September included in the rental rate!

 

Pool Heated to 80  May, June & September weeks at additional cost ($400). 

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ROSKH

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Property Details
East Chop Classic Waterfront Home, Private Dock, Mooring Available, Spectacular Sunsets

Experience the epitome of summer living at East Chop Oak Bluffs in this delightful waterfront retreat. Nestled amidst the serenity of the beachfront, this cozy home boasts a private dock...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$6,000 - $10,000
June 2025
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August 2025
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 $8,000
September 2025
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$6,000
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$6,000
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 $6,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
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MILTD

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Property Details
Perfect in Town Location. Just 1 to 2 blocks to Beach, Town Center & Harbor Area, Walk to and from the Ferry

Centrally located in the heart of Oak Bluffs, walk 1-2 blocks to the beach, public tennis courts, and town & harbor areas. This wonderful large home has a large wrap-around porch for relaxing, 7...Read more

Location: 
Oak Bluffs
Sleeps: 
14
Bedrooms: 
7
Baths: 
3
Price Range:
$8,500 - $9,500
June 2025
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August 2025
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$12,500
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 $9,500
September 2025
SuMoTuWeThFrSaWeek
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$9,500
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$9,500
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 $8,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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CORSB

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Property Details
Outstanding Waterfront Home, Private Dock, Spectacular Views & Sunsets across and up the Lagoon. Screened Porch, Larger Wrap Around Deck with Cushioned Chaise and Chair Seating

Nestled hillside, this lovely contemporary residence offers an exquisite retreat overlooking the tranquil lagoon and the sunsets are magnificent. Featuring breathtaking water vistas, a private dock, a screened porch, an expansive...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$7,000 - $9,000
June 2025
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August 2025
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$7,000
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 $7,000
Clean Fee: 
$575 per week
Tax: State & Local: 
11.7
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COONC

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Property Details
The Boathouse, East Chop Location, Gorgeous Water and Sunset Views, Architect Designed Gem

Designed by a renowned island architect and custom-crafted,  The Boathouse underwent construction and total renovation in 2016 and is now a terrific year-round home.  The exterior of the house maintains...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
3
Baths: 
2
Price Range:
$4,400 - $9,000
June 2025
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$6,500
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 $4,500
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Two-week minimum stay per owner! 

 

 

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BROWL

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Property Details
Stunning Tri-Level Home, Heated Pool, Screened Porch, Beautifully Landscaped, Walk to Association Tennis Courts

Featured MVVR Listing:

Beautiful Coastal Inspired Retreat features multiple living spaces, a pool, a bluestone patio area, and a deck with an outdoor dining and grill area.  This beautiful home is...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$9,000 - $9,000
June 2025
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 $11,000
September 2025
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$9,000
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$9,000
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Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

Pool Heated to 80 degrees included in rental rate last Saturday in June to the first Saturday in September. 

 

Pool Heated to 80 degrees, June & September weeks additional $300 propane surcharge per week. 

   

 

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VANA2

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Property Details
Charming , Modern In-Town Oak Bluffs Vacation Home. Walk to Town, Parks, Beach. 4 Bedrooms, Sleeps 8, 3 Baths

This charming Oak Bluffs home is tucked away in a peaceful neighborhood, yet conveniently located just a 10-minute walk to the heart of town, the harbor, and the beach. Meticulously...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$70 - $8,500
June 2025
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 $7,000
August 2025
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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PRIAN

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Property Details
Beautiful Upscale Contemporary Home, Designer Details Throughout, 4 Bedrooms, 4.5 Baths, Muliple Living Areas

Discover this stunning tri-level vacation home nestled in a peaceful community just on the outskirts of Oak Bluffs and minutes away from Oak Bluffs center, Edgartown Village, downtown Vineyard Haven, and several...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
4
Price Range:
$7,600 - $8,400
June 2025
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July 2025
SuMoTuWeThFrSaWeek
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31
 $8,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$8,000
3
4
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$8,300
10
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$8,300
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$8,300
24
25
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$7,500
31
 
September 2025
SuMoTuWeThFrSa
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30
 
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
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BEG21

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Property Details
Ideally located just 1 mile to OB Center, Many Updates, Enclosed Private Back Yard, Deck Nicely outfitted with Dining and new Living Area Grouping., Central AC

This cozy recently updated vacation home is tucked on a quiet street just on the outskirts of Oak Bluffs Center. Bike or walk to the town center, Inkwell Beach, and the picturesque Harbor...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,500 - $8,000
June 2025
SuMoTuWeThFrSa
1
2
3
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July 2025
SuMoTuWeThFrSaWeek
 1
2
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13
14
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17
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21
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23
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26
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29
30
31
 $6,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,000
3
4
5
6
7
8
9
$8,000
10
11
12
13
14
15
16
$8,000
17
18
19
20
21
22
23
$8,000
24
25
26
27
28
29
30
$6,500
31
 $3,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,500
7
8
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13
$3,500
14
15
16
17
18
19
20
$3,500
21
22
23
24
25
26
27
$3,500
28
29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Note: Owner maintains security camera on front of house

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BURBR

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Property Details
Perfect Retreat for Large Families, 1.5 miles to Oak Bluffs Town Center & Beach, Bike Path at end of Street

Spacious and perfect for extended families, featuring multiple attractively furnished living areas, and sleeps 13 comfortably. The lower level of the house features a queen bed, kitchenette, den area with...Read more

Location: 
Oak Bluffs
Sleeps: 
11
Bedrooms: 
5
Baths: 
3
Price Range:
$7,350 - $7,950
June 2025
SuMoTuWeThFrSa
1
2
3
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9
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July 2025
SuMoTuWeThFrSaWeek
 1
2
3
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12
13
14
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21
22
23
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26
27
28
29
30
31
 $7,350
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,350
3
4
5
6
7
8
9
$7,350
10
11
12
13
14
15
16
$7,350
17
18
19
20
21
22
23
$7,950
24
25
26
27
28
29
30
$7,950
31
 $7,350
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,350
7
8
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13
$7,350
14
15
16
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20
$7,350
21
22
23
24
25
26
27
$7,350
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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INGAE

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Property Details
Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$4,630 - $7,750
June 2025
SuMoTuWeThFrSa
1
2
3
4
5
6
7
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9
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July 2025
SuMoTuWeThFrSaWeek
 1
2
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12
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14
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16
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21
22
23
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25
26
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29
30
31
 $11,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$11,000
3
4
5
6
7
8
9
$11,000
10
11
12
13
14
15
16
$11,000
17
18
19
20
21
22
23
$11,000
24
25
26
27
28
29
30
$11,000
31
 $7,750
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,750
7
8
9
10
11
12
13
$7,000
14
15
16
17
18
19
20
$6,900
21
22
23
24
25
26
27
$6,800
28
29
30
 $6,700
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Rates reduce for available weeks in June & July - see calendar for adjusted rates

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